1. Field of the Invention
This invention relates to novel compounds, trichloropolyfluoro-bicyclo ethres, suitable as solvents or thermal media and to a method for the manufacture of the compounds.
2. Description of the Prior Art
Polychloropolyfluoro-monocyclo ethers have been known to the art. As techniques for the manufacture of these compounds, there have been suggested (1) a method which resorts to chlorination of polyfluoro-monocycle ether (J. Am. Chem. Soc., Vol. 74, page 5420) and (2) a method which involves chlorination of perfluoro-monocyclo ether (J. Am. Chem. Soc., Vol. 77, page 4837), for example. To be specific, the method of (1) comprises photochemically chlorinating an .alpha.,.alpha.,.alpha.',.alpha.'-tetrahydroperfluoro-monocyclo ether and the method of (2) comprises chlorinating a monocyclic perfluoro ether by the agency of anhydrous aluminum chloride.
Polychloropolyfluoro-bicyclo ethers which have a bicyclic configuration have not heretofore been known to the art.
The inventors of this invention conducted various studies on production of perfluoro compounds having a bicyclic configuration. They consequently succeeded in producing novel perfluoro-bicyclo ethers such as perfluoro-(7-oxa-bicyclo[4.3.0]nonane) and perfluoro-(2-oxa-bicyclo[3.3.0]octane) by electrolytically fluorinating a monocarboxylic acid having a cyclohexyl group or cyclopentyl group attached to an .alpha.-carbon atom thereof or a derivative of the carboxylic acid (Japanese Patent Publication No. SHO 55(1980)-045547 and No. SHO 55(1980)-032794). After further studies in the same field, they have now ascertained that the reaction of anhydrous aluminum chloride upon such a perfluoro-cyclo ether unexpectedly produces a novel partially chlorinated compound. The present invention has issued from this knowledge.